The Bootstrapped Founder

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public..

Author: Arvid Kahl

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.
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Language: en

Genres: Business, Entrepreneurship, Marketing

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431: Many Heads, Not Many Hats: The Founder's Identity Crisis
Friday, 9 January, 2026

We joke about founders wearing many hats, but that metaphor misses the point. It's not about swapping accessories—it's about growing entirely new heads, each with its own brain that thinks, speaks, and prioritizes differently. In this episode, I explore why the transition from consulting or agency work to software entrepreneurship is so disorienting, and why the instincts that made you successful before might be the exact things preventing success now. From the uncomfortable truth about acquisition in low-touch SaaS to the cognitive dissonance of believing in yourself while questioning everything you know, this is about what it really takes to become someone new while staying grounded in who you've always been.This episode of The Bootstraped Founder is sponsored by Paddle.comThe blog post: https://thebootstrappedfounder.com/many-heads-not-many-hats-the-founders-identity-crisis/ The podcast episode: https://tbf.fm/episodes/many-heads-not-many-hats-the-founders-identity-crisisCheck out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw